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3-Aminoquinoline → HCID 86685608, 화합물

HRID 2200491
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HRID 2200491 반응식
Cl[C:2]1[N:7]=[C:6]([NH:8][C@H:9]([CH:13]([CH3:15])[CH3:14])[C:10]([NH2:12])=[O:11])[CH:5]=[N:4][C:3]=1[C:16]#[N:17].N[C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2.C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.CC([O-])=O.CC([O-])=O.[Pd+2]>[C:16]([C:3]1[N:4]=[CH:5][C:6]([NH:8][C@H:9]([CH:13]([CH3:15])[CH3:14])[C:10]([NH2:12])=[O:11])=[N:7][C:2]=1[C:19]1[CH:20]=[N:21][C:22]2[C:27]([CH:28]=1)=[CH:26][CH:25]=[CH:24][CH:23]=2)#[N:17]
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참가 물질

7

반응물 4

HCID 113753-AminoquinolineHCID 11430Potassium CarbonateHCID 634876Binap, (A+-)-HCID 86685607(R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-methylbutanamide

생성물 1

HCID 86685608HCID 86685608, 화합물수율 82.8%

시약·촉매·용매 2

HCID 167845
palladium(II) acetate
촉매
HCID 312751,4-Dioxane용매

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온도
95 °C

실험 절차

To a mixture of (R)-2-(6-chloro-5-cyanopyrazin-2-ylamino)-3-methylbutanamide (100 mg, 0.394 mmol) in Dioxane (2 mL) was added 3-aminoquinoline (71 mg, 0.492 mmol), Pd(OAc)2 (18 mg, 0.079 mmol), BINAP (49 mg, 0.079 mmol) and K2CO3 (163 mg, 1.18 mmol). After heating at 95° C. for 5 h, the mixture was filtered, the filtrate was concentrated and purified by preparative HPLC to give (R)-2-(5-cyano-6-(quinolin-3-yl)pyrazin-2-ylamino)-3-methylbutanamide (113 mg).

후처리

  1. filtrationthe mixture was filtered
  2. concentrationthe filtrate was concentrated
  3. custompurified by preparative HPLC

출처 및 근거

ORD 기록
ord-d2719151161843cdbf08c4b792532a8f
출처 데이터셋
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09359308B2

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